A Copper-Catalyzed Interrupted Domino Reaction for the Synthesis of Fused Triazolyl Benzothiadiazine-1-oxides

被引：3

作者：

Hommelsheim, Rene ^{[1
]}

Bausch, Sandra ^{[1
]}

Selvakumar, Arjuna ^{[1
]}

Amer, Mostafa M. ^{[1
,2
]}

Truong, Khai-Nghi ^{[3
]}

Rissanen, Kari ^{[3
]}

Bolm, Carsten ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Egyptian Petr Res Inst, Cairo 11727, Egypt

[3] Univ Jyvaskyla, Dept Chem, POB 35, Survontie 9 B, Jyvaskyla 40014, Finland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 13期

关键词：

CLICK; copper catalysis; cycloaddition; domino reactions; sulfoximines; sulfur heterocycles; ONE-POT SYNTHESIS; CLICK CHEMISTRY; ORGANIC AZIDES; HETEROCYCLIC CHEMISTRY; NITROGEN-HETEROCYCLES; ARYLATION SEQUENCE; TERMINAL ALKYNES; NATURAL-PRODUCTS; SULFOXIMINES; 1,2,3-TRIAZOLES;

D O I：

10.1002/chem.202203729

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Copper(I)-catalyzed domino reactions of 2-azido sulfoximines with 1-iodoalkynes yield fused triazolyl-containing benzothiadiazine-1-oxides. The protocol features the synthesis of two fused heterocyclic rings in one step with good to excellent yields and a broad functional group tolerance. Detailed mechanistic investigations indicate that a copper pi-complex initiates a cycloaddition and oxidative C-N coupling reaction sequence. The results suggest an interrupted domino process involving an iodinated triazole as a key intermediate.

引用

页数：7

共 50 条

[41] Copper-Catalyzed 2:1 Coupling Reaction of Arynes with Alkynes
Yoshida, Hiroto
Morishita, Takami
Nakata, Hiromi
Ohshita, Joji
ORGANIC LETTERS, 2009, 11 (02) : 373 - 376
[42] Harnessing In Situ Radical Oxygenation: Copper-Catalyzed Interrupted Azirine-Alkyne Ring-Expansion Reaction for the Synthesis of Pyrrolones
Sujatha, Chandragiri
Nallagangula, Madhu
Namitharan, Kayambu
ORGANIC LETTERS, 2021, 23 (11) : 4219 - 4223
[43] Asymmetric Synthesis of Spirocyclic-Lactams through Copper-Catalyzed Kinugasa/Michael Domino Reactions
Shu, Tao
Zhao, Long
Li, Sun
Chen, Xiang-Yu
von Essen, Carolina
Rissanen, Kari
Enders, Dieter
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (34) : 10985 - 10988
[44] Copper-Catalyzed Domino Addition-Cyclization Reaction between Terminal Alkynes, Carbon Disulfide, and Oxiranes
Ghazanfarpour-Darjani, Majid
Babapour-Kooshalshahi, Mahboobeh
Mousavi-Safavi, Seyed Mahmoud
Akbari-Neyestani, Jafar
Khalaj, Mehdi
SYNLETT, 2016, 27 (02) : 259 - 261
[45] Copper-catalyzed three-component reaction for the synthesis of fluoroalkoxyl imidates
Wang, Zeng
Ding, Xinzhi
Li, Shiwei
Weng, Zhiqiang
TETRAHEDRON, 2018, 74 (46) : 6631 - 6634
[46] Development of a general copper-catalyzed vinylic Finkelstein reaction-application to the synthesis of the C1-C9 fragment of laingolide B
Nitelet, Antoine
Jouvin, Kevin
Evano, Gwilherm
TETRAHEDRON, 2016, 72 (40) : 5972 - 5987
[47] Copper(I)-Catalyzed Interrupted Click Reaction: Synthesis of 1,4,5-Trisubstituted 5-Chloro-1,2,3-Triazoles
Wu, Qiming
Song, Wangze
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (42)
[48] Unexpected Copper-Catalyzed Cascade Reaction of 1,6-Enynes with Sulfoxonium Ylides
Zhang, Hong
He, Jieyin
Xu, Wendi
Yang, Liangliang
Zhang, Xue
Wang, Haiyang
Lang, Ming
Wang, Jian
Peng, Shiyong
ORGANIC LETTERS, 2022, 24 (39) : 7095 - 7100
[49] Synthesis of pyrazolo[1,5-c]quinazoline derivatives through the copper-catalyzed domino reaction ofo-alkenyl aromatic isocyanides with diazo compounds
Liu, Lu
Li, Lei
Mao, Shukuan
Wang, Xin
Zhou, Ming-Dong
Zhao, Yu-long
Wang, He
CHEMICAL COMMUNICATIONS, 2020, 56 (55) : 7665 - 7668
[50] Selective Synthesis of 2-(1,2,3-Triazoyl) Quinazolinones through Copper-Catalyzed Multicomponent Reaction
Sacramento, Manoela
Piuma, Luis Pedro A.
Nascimento, Jose Edmilson R.
Cargnelutti, Roberta
Jacob, Raquel G.
Lenardao, Eder Joao
Alves, Diego
CATALYSTS, 2021, 11 (10)

← 1 2 3 4 5 →